During my senior year of high school, I met with Ms. Allen, the school's guidance counselor. She asked me if I had any career plans after graduation. I told her that I didn't have anything in mind at the time. She looked over my grades, shook her head, and smiled.

Mrs. Allen was approximately in her forties. Although she dressed conservatively, I'm sure in her younger years, she had many offers for dates or other ideas involving sex. Her looks remained as if she were ten years younger, with shoulder-length, brunette hair, brown eyes behind her glasses, probably thirty-six D breasts, and matching waist size.

I've heard talk from the football players saying she was a MILF.

"Parker, you have decent grades, but if I were to recommend college; you'd probably tell me it would be a waste of your time."

I laughed and said, "Ms. Allen, you're correct. I'd rather go to trade school or something."

Ms. Allen leaned back in her chair and asked me about things I enjoyed. I said my family took vacations every summer to different places. She asked if my family drove or flew to those places. I said we did both.

She thought about my answer for a moment, then told me about a trip she had planned during the summer.

"Parker, I am going to Europe in June. I’m going to Paris for the third time. I've been to many places in my lifetime, and I love to travel. When I was your age, I became a stewardess. I worked for a large airline for a while, to pay for college. Those were some fun times." She sighed slightly, as she reminisced.

She paused to let her words sink in, then continued.

"You have the world in front of you and you should take my advice. You could do good in a career as that. From there, you'll meet many interesting people and go to many more interesting places than you can imagine."

That piqued my interest and Ms. Allen showed me some information regarding many of the regional airlines. She talked about the classes I would attend and read over the courses required. She determined I could handle them with relative ease.

To my surprise, Ms. Allen found some applications online, then assisted me with filling out the applications to four airlines. A few times, she leaned over my shoulder, to point out a reply on my applications. I felt her breasts or her warm breath on my neck.

I was getting aroused.

When we finished, I thanked her and let her know when I received any notices.

A few weeks passed, and I got a favorable letter from a large airline. They requested I attend their next training, which would be starting soon. I told Ms. Allen about it, and she said to wait about a week, to see if any others responded.

She said, "However, this is likely your best offer."

I responded to that airline, and soon my application was accepted. I graduated high school and prepared to leave home for about two months.

After approximately eight weeks of training in another state, I was assigned to stateside flights. The first flights I was assigned to, I had a female mentor named Charlotte. She was about twenty years older, blonde hair and blue eyes. She was nice and liked to have fun with the rest of the crew and the passengers.

I learned a lot from Charlotte and soon, I was reassigned to another flight crew.

We’ve heard stories about sex within the airline industry, but it isn’t all true. The hours are long, and when we check into a hotel somewhere, we’re tired and want to get off our feet. And the days begin early.

However, I have had advances from many women, from stewards, passengers, and pilots.

So, let’s begin.

My first sexual encounter was with a woman named Sandra.

Sandra was about five years older, with shoulder-length blonde hair. She had grey eyes, and small breasts. I found her interesting, because her personality came across as she didn’t like to be messed with. Sometimes she seemed distant, other times funny.

She was on a flight I worked on that flew some small routes, meaning smaller regional airports, interconnecting with each other, then we would fly to one of the larger, international airports.

We had a stopover in a small southern city, the only night stop on this schedule.

The morning flight started off normally, and Sandra was in a good mood, interacting with the passengers. While we were setting up the snack carts, she made comments regarding some of the passengers.

She pointed out a couple, who reminded her of some cartoon characters and had me serve the section of the plane where they sat. I couldn’t help but have a smile when I saw them and had to control myself when I did reach their seats.

As we collected the trash, before landing, I told Sandra she was bad. She smiled, and said, “You haven’t seen anything, yet!”

I eyed her for a second because I wasn’t certain of what to expect. Was she about to go off on someone?

Yes. 

The rest of the day, Sandra was in a happy mood. Now and then, she would brush up against me, in a discreet, but provocative way. Once or twice, she would rub my crotch or ass.

When we reached our hotel, Sandra held me back from the check-in desk until the pilots finished registering. While the pilots were walking to their rooms, we checked in.

Sandra managed to have our rooms adjoining, with doors that joined our rooms.

I settled in, turned on the television, took a long warm shower, then wrapped a towel around my waste. I went to the bed, sat on it, and checked my phone for any messages or missed calls.

As I was perusing the television channels, Sandra began tapping on the adjoining doors.

I forgot I was wearing the towel and I called out, “Just a minute, I’m not dressed!”

Sandra replied, “Open up, I don’ like to waste time!”

Clad only in a towel, I opened the door, and saw Sandra, holding a couple of beers and wearing an oriental robe that didn’t cover her white panties.

“These were getting a bit warm. I knocked earlier.” She said as she handed me one of the beers.

“I was taking a shower.” I deadpanned, almost dropping the towel.

Sandra caught the slight, and said, “You work fast, don’t you?” And she moved toward the bed.

I grinned, and said, “No sense in wasting time.”

After I took a long sip of the beer, Sandra took it from me, set it on the bedside table, and turned off the television. As I walked toward her, she put her arms around my shoulders, and we began to kiss.

Naturally, the towel dropped and when it hit our feet, Sandra turned off the bedside lamp, rolled me onto the bed, and began to suck my hard cock. She had good oral talent, and it took as much stamina as I could muster to prevent giving her my load.

Before she reached my point of no return, I rolled her off me, and her robe opened, showing me her small breasts. Sandra had small, hard nipples and apparently, they were sensitive.

I licked and sucked on them, and she began to get aroused. She managed to get her panties off while I was giving her nipples all my attention.

Then I put one of my hands between her thighs and didn’t feel any pubic hair.

Nice, I love eating bare pussy.

I didn’t waste time getting there and Sandra didn’t take long to begin having orgasms.

And she had several in rapid successions.

When she couldn’t take any more of my tongue lashings and fingering, I mounted on top of her and began to slowly push inside her wet pussy.

Sandra relaxed and after I pushed a few strokes inside her, she began to tighten her muscles.

I continued a few more minutes on top of her, then coaxed her onto her knees, so I could get some from behind.

Hidden beneath Sandra’s uniform is a small, round ass that I’d love to eat on more than one occasion. The sight of it, just as I was about to penetrate it, had me in another level of arousal.

As I was thrusting myself, I put my thumb on her anus, and this put Sandra on another plane of arousal, too.

The heightened sex had both of us climaxing simultaneously and after a few moments of ecstasy, had us gasping for breath, as we lay beside each other on the wet bed sheets.

Sandra caught her breath after a few minutes, rolled over to kiss me, then got up.

Finding her robe, as she was leaving the dark room, I heard her say, “The day begins early, sailor.”

Sailor?